Synthesis and structure-activity relationships of novel benzoxaboroles as a new class of antimalarial agents

Bioorg Med Chem Lett. 2011 Jan 15;21(2):644-51. doi: 10.1016/j.bmcl.2010.12.034. Epub 2010 Dec 10.

Abstract

A series of boron-containing benzoxaborole compounds was designed and synthesized for a structure-activity relationship investigation surrounding 7-(HOOCCH(2)CH(2))-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1) with the goal of discovering a new antimalarial treatment. Compound 1 demonstrates the best potency (IC(50)=26nM) against Plasmodium falciparum and has good drug-like properties, with low molecular weight (206.00), low ClogP (0.86) and high water solubility (750μg/mL at pH 7).

MeSH terms

  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry*
  • Antimalarials / pharmacology*
  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry*
  • Boron Compounds / pharmacology*
  • Cell Line
  • Cell Survival / drug effects
  • Humans
  • Malaria, Falciparum / drug therapy*
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Boron Compounds